Organic molecules for use in optoelectronic devices

ABSTRACT

An organic molecule for use in optoelectronic components is disclosed having a structure of Formula IwithX=CN or CF3,D=wherein# is the point of attachment of unit D to one of the phenyl rings shown in Formula I;Z is a direct bond or is selected from the group consisting of CR3R4, C═CR3R4, C═O, C═NR3, NR3, O, SiR3R4, S, S(O) and S(O)2;In each occurrence R1 and R2 is the same or different, is H, deuterium, a linear alkyl group having 1 to 5 C atoms, a linear alkenyl or alkynyl group having 2 to 8 C atoms, a branched or cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, wherein one or more H atoms can be replaced by deuterium, or an aromatic or heteroaromatic ring system having 5 to 15 aromatic ring atoms, which can in each case be substituted with one or more radicals R6;and wherein at least one Ra is not H, andwherein at least one R2 is H.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority under 35 U.S.C. § 371 to InternationalApplication No. PCT/EP2017/065225, filed Jun. 21, 2017 which claims thebenefit of DE 10 2016 112 078.2 filed Jul. 1, 2016, and entitled“ORGANIC MOLECULES, IN PARTICULAR FOR USE IN OPTOELECTRONIC DEVICES”,the disclosures of which are incorporated by reference herein in theirentireties.

FIELD OF INVENTION

The invention relates to purely organic molecules and the use thereof inorganic light-emitting diodes (OLEDs) and in other organicoptoelectronic devices.

BRIEF DESCRIPTION OF THE DRAWINGS

Exemplary embodiments of the present invention will be described belowin more detail, with reference to the accompanying drawings, of which:

FIG. 1 is an Emission spectrum of Example 1 in 10% PMMA.

FIG. 2 is an Emission spectrum of Example 2 in 10% PMMA.

FIG. 3 is an Emission spectrum of Example 3 in 10% PMMA.

FIG. 4 is an Emission spectrum of Example 4 in 10% PMMA.

FIG. 5 is an Emission spectrum of Example 5 in 10% PMMA.

FIG. 6 is an Emission spectrum of Example 6 in 10% PMMA.

DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS OF THE INVENTION

Exemplary embodiments of the invention will now be discussed in furtherdetail. This invention may, however, be embodied in many different formsand should not be construed as limited to the embodiments set forthherein.

The underlying task of the present invention was to provide moleculeswhich are suitable for use in optoelectronic devices.

The invention provides a new class of organic molecules, which aresuitable for use in organic optoelectronic devices.

The organic molecules according to the invention are purely organicmolecules; i.e. they do not have any metal ions, and thus differ fromthe metal complex compounds known for use in organic optoelectronicdevices.

The organic molecules according to the invention are characterized byemissions in the blue, sky blue, or green spectral range. Thephotoluminescence quantum yields of the organic molecules according tothe invention are in particular 20% and more. The molecules according tothe invention in particular exhibit thermally activated delayedfluorescence (TADF). The use of the molecules according to the inventionin an optoelectronic device, for example an organic light-emitting diode(OLED), results in higher efficiencies of the device. CorrespondingOLEDs have a higher stability than OLEDs having known emitter materialsand comparable color.

The blue spectral range here is understood to be the visible range from430 nm to 470 nm. The sky blue spectral range here is understood to bethe range between 470 nm and 499 nm. The green spectral range here isunderstood to be the range between 500 nm and 599 nm. The emissionmaximum is in the respective range.

The organic molecules have a structure of Formula I or consist of astructure according to Formula I:

with

-   -   X=CN or CF₃,    -   D=

-   -   # is the point of attachment of unit D to one of the phenyl        rings shown in Formula I.    -   Z is a direct bond or is selected from the group consisting of        CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O, SiR³R⁴, S, S(O), S(O)₂.    -   In each occurrence R¹ and R² is the same or different, is H,        deuterium, a linear alkyl group having 1 to 5 C atoms, a linear        alkenyl or alkynyl group having 2 to 8 C atoms, a branched or        cyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms,        wherein one or more H atoms can be replaced by deuterium or an        aromatic ring system having 5 to 15 aromatic ring atoms, which        can in each case be substituted with one or more radicals R⁶.    -   In each occurrence R^(a), R³ and R⁴ is the same or different, is        H, deuterium, N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F,        Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40        C atoms or a linear alkenyl or alkynyl group having 2 to 40 C        atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or        thioalkoxy group having 3 to 40 C atoms, which can in each case        be substituted with one or more radicals R⁵, wherein one or more        non-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C,        Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO,        SO₂, NR⁵, O, S or CONR⁵ and wherein one or more H atoms can be        substituted with deuterium, CN, CF₃ or NO₂; or an aromatic or        heteroaromatic ring system having 5 to 60 aromatic ring atoms,        which can in each case be substituted with one or more radicals        R⁵, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic        ring atoms, which can be can be substituted with one or more        radicals R⁵, or a diarylamino group, diheteroarylamino group or        arylheteroarylamino group having 10 to 40 aromatic ring atoms,        which can be substituted with one or more radicals R⁵.    -   In each occurrence R⁵ is the same or different, is H, deuterium,        N(R⁶)₂, OH, Si(R⁶)₃, B(OR⁶)₂, OSO₂R⁶, CF₃, CN, F, Br, I, a        linear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms        or a linear alkenyl or alkynyl group having 2 to 40 C atoms or a        branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy        group having 3 to 40 C atoms, which can in each case be        substituted with one or more radicals R⁶, wherein one or more        non-adjacent CH₂ groups can be replaced by R⁶C═CR⁶, C≡C,        Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO,        SO₂, NR⁶, O, S or CONR⁶ and wherein one or more H atoms can be        substituted with deuterium, CN, CF₃ or NO₂; or an aromatic or        heteroaromatic ring system having 5 to 60 aromatic ring atoms,        which can in each case be substituted with one or more radicals        R⁶, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic        ring atoms, which can be substituted with one or more radicals        R⁶, or a diarylamino group, diheteroarylamino group or        arylheteroarylamino group having 10 to 40 aromatic ring atoms,        which can be substituted with one or more radicals R⁶.    -   In each occurrence R⁶ is the same or different, is H, deuterium,        OH, CF₃, CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy        group having 1 to 5 C atoms or a linear alkenyl or alkynyl group        having 2 to 5 C atoms or a branched or cyclic alkyl, alkenyl,        alkynyl, alkoxy or thioalkoxy group having 3 to 5 C atoms,        wherein one or more H atoms can be replaced by deuterium, CN,        CF₃ or NO₂; or an aromatic or heteroaromatic ring system having        5 to 60 aromatic ring atoms or an aryloxy or heteroaryloxy group        having 5 to 60 aromatic ring atoms or a diarylamino group,        diheteroarylamino group or arylheteroarylamino group having 10        to 40 aromatic ring atoms.    -   Each of the radicals R^(a), R³, R⁴ or R⁵ can also form a mono-        or polycyclic, aliphatic, aromatic and/or benzoannelated ring        system with one or more further radicals R^(a), R³, R⁴ or R⁵.    -   According to the invention, at least one R^(a) is not H and at        least one R² is H.

In another embodiment, R¹ is H or methyl and R² is H.

In a further embodiment, both X are CN.

In one embodiment of the organic molecules, the two Groups D areidentical; in another embodiment, the two Groups D are different.

In another embodiment of the organic molecules, one Group D or bothGroups D has or have a structure of Formula IIa or consist(s) of astructure of Formula IIa:

wherein the abovementioned definitions apply for # and R^(a).

In another embodiment of the organic molecules according to theinvention, one Group D or both Groups D have(s) a structure of FormulaIIb, Formula IIb-2 or Formula IIb-3 or consist(s) thereof:

wherein

-   -   In each occurrence R^(b) is the same or different, is N(R⁵)₂,        OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I, a linear alkyl,        alkoxy or thioalkoxy group having 1 to 40 C atoms or a linear        alkenyl or alkynyl group having 2 to 40 C atoms or a branched or        cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group        having 3 to 40 C atoms, which can in each case be substituted        with one or more radicals R⁵, wherein one or more non-adjacent        CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R5)2, ^(Ge(R)5)2,        ^(SN(R)5)2, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S        or CONR⁵ and wherein one or more H atoms can be substituted with        deuterium, CN, CF₃ or NO₂; or an aromatic or heteroaromatic ring        system having 5 to 60 aromatic ring atoms, which can in each        case be substituted with one or more radicals R⁵, or an aryloxy        or heteroaryloxy group having 5 to 60 aromatic ring atoms, which        can be substituted with one or more radicals R⁵, or a        diarylamino group, diheteroarylamino group or        arylheteroarylamino group having 10 to 40 aromatic ring atoms,        which can be substituted with one or more radicals R⁵.    -   Otherwise, the above-mentioned definitions apply.

In another embodiment of the organic molecules according to theinvention, one Group D has or both Groups D have a structure of FormulaIIc, Formula IIc-2 or Formula IIc-3 or consist(s) thereof:

wherein the abovementioned definitions apply.

In a further embodiment of the organic molecules according to theinvention, in each occurrence R^(b) is independently selected from thegroup consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which can in eachcase be substituted with one or more radicals selected from Me, ^(i)Pr,^(t)Bu, CN, CF₃ or Ph, pyridinyl, pyrimidinyl, carbazolyl, which can ineach case be substituted with one or more radicals selected from Me,^(i)Pr, ^(t)Bu, CN, CF₃, or Ph, and N(Ph)₂.

Embodiments of Group D are shown in the following as examples:

wherein the abovementioned definitions apply for #, Z, R^(a) and R⁵. Inone embodiment, in each occurrence, the radical R⁵ is the same ordifferent and is selected from the group consisting of H, methyl, ethyl,phenyl and mesityl.

In one embodiment, in each occurrence, the radical R^(a) is the same ordifferent and is selected from the group consisting of H, methyl (Me),i-propyl (CH(CH₃)₂) (^(i)Pr), t-butyl (^(t)Bu), phenyl (Ph), CN, CF₃ anddiphenylamine (NPh₂), wherein at least R^(a) is not H.

In the context of this invention, an aryl group contains 6 to 60aromatic ring atoms; a heteroaryl group contains 5 to 60 aromatic ringatoms, at least one of which represents a heteroatom. The heteroatomsare, in particular, N, O and/or S. In the event that other definitions,which differ from the stated definitions, for example with respect tothe number of aromatic ring atoms or the contained heteroatoms, arespecified in the description of specific embodiments of the invention,then these definitions apply.

An aryl group or heteroaryl group is understood to be a simple aromaticring, i.e. benzene, or a simple heteroaromatic ring, for examplepyridine, pyrimidine or thiophene, or a heteroaromatic polycycliccompound, for example phenanthrene, quinoline or carbazole. In thecontext of the present application, a condensed (annelated) aromatic orheteroaromatic polycyclic compound consists of two or more simplearomatic or heteroaromatic rings which are condensed with one another.

An aryl or heteroaryl group, which can in each case be substituted withthe abovementioned radicals and which can be linked to the aromatic orheteroaromatic group via any desired positions, are in particularunderstood to be groups which are derived from benzene, naphthalene,anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene,fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene,benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene,benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole,isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine,phenanthridine, benzo-5,6-quinoline, isoquinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthimidazole, phenanthrimidazole,pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole,benzoxazole, napthoxazole, anthroxazole, phenanthroxazole, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine,naphthyridine, azacarbazole, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine,pteridine, indolizine and benzothiadiazole or combinations of saidgroups.

A cyclic alkyl, alkoxy or thioalkoxy group is understood here to be amonocyclic, a bicyclic or a polycyclic group.

Within the scope of the present invention, a C₁ to C₄₀ alkyl group, inwhich individual H atoms or CH₂ groups can also be substituted by thegroups mentioned above, are understood to be, for example, the radicalsmethyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl,t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl,2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluorethyl,2,2,2-trifluorethyl, 1,1-dimethyl-n-hex-1-yl-,1,1-dimethyl-n-hept-1-yl-, 1,1-dimethyl-n-oct-1-yl-,1,1-dimethyl-n-dec-1-yl-, 1,1-dimethyl-n-dodec-1-yl-,1,1-dimethyl-n-tetradec-1-yl-, 1,1-dimethyl-n-hexadec-1-yl-,1,1-dimethyl-n-octadec-1-yl-, 1,1-diethyl-n-hex-1-yl-,1,1-diethyl-n-hept-1-yl-, 1,1-diethyl-n-oct-1-yl-,1,1-diethyl-n-dec-1-yl-, 1,1-diethyl-n-dodec-1-yl-,1,1-diethyl-n-tetradec-1-yl-, 1,1-diethyln-n-hexadec-1-yl-,1,1-diethyl-n-octadec-1-yl-, 1-(n-propyl)-cyclohex-1-yl-,1-(n-butyl)-cyclohex-1-yl-, 1-(n-hexyl)-cyclohex-1-yl-,1-(n-octyl)-cyclohex-1-yl- and 1-(n-decyl)-cyclohex-1-yl. An alkenylgroup is understood to be ethenyl, propenyl, butenyl, pentenyl,cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl,cyclooctenyl or cyclooctadienyl, for example. An alkynyl group isunderstood to be ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynylor octynyl, for example. A C₁ to C₄₀ alkoxy group is understood to bemethoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy, for example.

One embodiment of the invention relates to organic molecules, which havean ΔE(S₁-T₁) value between the lowest excited singlet (S₁) state and thetriplet (T₁) state below it that is no higher than 5000 cm⁻¹, inparticular no higher than 3000 cm⁻¹, or no higher than 1500 cm⁻¹ or 1000cm⁻¹ and/or an emission lifetime of at most 150 μs, in particular atmost 100 μs, at most 50 μs, or at most 10 μs and/or a main emission bandhaving a full width at half maximum (FWHM) of less than 0.55 eV, inparticular less than 0.50 eV, less than 0.48 eV, or less than 0.45 eV.

The organic molecules according to the invention in particular have anemission maximum between 430 and 520 nm, between 440 and 495 nm orbetween 450 and 470 nm.

Due to the position of the emission maximum in the named region, theorganic molecules according to the invention are suitable for use indisplays, in particular in ultra-high definition displays, in particulartelevisions (UHDTVs). The color space of a UHDTV is determined accordingto the so-called Rec. 2020 Recommendation (Recommendation ITU-R BT.2020)via the primary colors. For blue, the optimum color point lies at aCIE_(x) coordinate of 0.131 and a CIE_(y) coordinate of 0.046. At a fullwidth at half maximum of the blue emission band of 0 nm, thiscorresponds to an emission maximum of 467 nm. As the full width at halfmaximum increases, the optimum emission maximum for the blue primarycolor according to Rec. 2020 occurs at shorter wavelengths, e.g. at 464nm for a full width at half maximum of 35 nm. Potential emission changescaused by other components of the display are not taken into account forthis value. An ideal blue emitter for UHDTV applications therefore hasan emission maximum between 450 and 470 nm.

The molecules in particular have a “blue material index” (BMI), thequotient of the PLQY (in %) and the CIE_(y) color coordinate of thelight emitted by the molecule according to the invention, that isgreater than 120, in particular greater than 200, greater than 250 orgreater than 300.

In a further aspect, the invention relates to a method for producing anorganic molecule according to the invention of the type described here(with a possible subsequent reaction), wherein a in 6 positionR¹-substituted and in 3 and 5 position R²-substituted2-bromo-4-fluorobenzonitrile or a in 6 position R¹-substituted and in 3and 5 position R²-substituted 2-bromo-4-fluorobenzotrifluoride is usedas the educt.

In one embodiment, the corresponding coupling reactant is produced byreacting in 6 position R¹-substituted and in 3 and 5 positionR²-substituted 2-bromo-4-fluorobenzonitrile or in 6 positionR¹-substituted and in 3 and 5 position R²-substituted2-bromo-4-fluorobenzotrifluoride with bis(pinacolato)diboron(4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane) in situ,and converted in a palladium-catalyzed cross-coupling reaction. Theproduct is obtained by deprotonation of the corresponding amine andsubsequent nucleophilic substitution of the fluorine groups. To do this,a nitrogen heterocyclic compound is reacted with an educt E1 in thecontext of a nucleophilic aromatic substitution. Typical conditionsinclude the use of a base, such as potassium phosphate tribasic orsodium hydride, in an aprotic polar solvent, such as dimethyl sulfoxide(DMSO) or N,N-dimethylformamide (DMF).

In a further aspect, the invention relates to the use of the organicmolecules as luminescent emitters or as host material in an organicoptoelectronic device, in particular wherein the organic optoelectronicdevice is selected from the group consisting of:

-   -   organic light-emitting diodes (OLEDs),    -   light-emitting electrochemical cells,    -   OLED sensors, in particular in gas and vapor sensors which are        not hermetically shielded to the outside,    -   organic diodes,    -   organic solar cells,    -   organic transistors,    -   organic field-effect transistors,    -   organic lasers and    -   down-conversion elements.

In a further aspect, the invention relates to a composition comprisingor consisting of:

-   (a) at least one organic molecule according to the invention, in    particular as an emitter and/or host, and-   (b) at least one, i.e. one or more emitter and/or host materials,    that is or are different from the organic molecule according to the    invention, and-   (c) optionally one or more dyes and/or one or more organic solvents.

In one embodiment, the composition according to the invention consistsof an organic molecule according to the invention and one or more hostmaterials. In particular, the host material or materials possess triplet(T₁) and singlet (S₁) energy levels, which are energetically higher thanthe triplet (T₁) and singlet (S₁) energy levels of the organic moleculeaccording to the invention. In one embodiment, in addition to theorganic molecule according to the invention, the composition has anelectron-dominant and a hole-dominant host material. The highestoccupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of thehole-dominant host material are in particular energetically higher thanthat of the electron-dominant host material. The HOMO of thehole-dominant host material is energetically below the HOMO of theorganic molecule according to the invention, while the LUMO of theelectron-dominant host material is energetically above the LUMO of theorganic molecule according to the invention. In order to avoid exciplexformation between emitter and host material or host materials, thematerials should be selected such that the energy distances between therespective orbitals are small. The distance between the LUMO of theelectron-dominant host material and the LUMO of the organic moleculeaccording to the invention is in particular less than 0.5 eV, preferablyless than 0.3 eV, even more preferably less than 0.2 eV. The distancebetween the HOMO of the hole-dominant host material and the HOMO of theorganic molecule according to the invention is in particular less than0.5 eV, preferably less than 0.3 eV, even more preferably less than 0.2eV.

In a further aspect, the invention relates to an organic optoelectronicdevice which has an organic molecule according to the invention or acomposition according to the invention. The organic optoelectronicdevice is in particular formed as a device selected from the groupconsisting of organic light-emitting diode (OLED); light-emittingelectrochemical cell; OLED sensor, in particular gas and vapor sensorswhich are not hermetically shielded to the outside; organic diode;organic solar cell; organic transistor; organic field-effect transistor;organic laser and down-conversion element.

An organic optoelectronic device comprising

-   -   a substrate,    -   an anode and    -   a cathode, wherein the anode or the cathode are disposed on the        substrate, and    -   at least one light-emitting layer, which is disposed between the        anode and the cathode and which has an organic molecule        according to the invention, represents a further embodiment of        the invention.

In one embodiment, the optoelectronic device is an OLED. A typical OLED,for example, has the following layer structure:

-   1. Substrate (supporting material)-   2. Anode-   3. Hole injection layer (HIL)-   4. Hole transport layer (HTL)-   5. Electron blocking layer (EBL)-   6. Emitting layer (EML)-   7. Hole blocking layer (HBL)-   8. Electron transport layer (ETL)-   9. Electron injection layer (EIL)-   10. Cathode.

The presence of specific layers is merely optional. Several of theselayers can also coincide. Specific layers can also be present more thanonce in the component.

According to one embodiment, at least one electrode of the organiccomponent is designed to be translucent. In this case, “translucent”describes a layer that is transmissive to visible light. The translucentlayer can be clearly translucent, i.e. transparent, or at leastpartially light-absorbing and/or partially light-diffusing, so that thetranslucent layer can, for example, also be diffusely or milkilytranslucent. A layer referred to here as translucent is in particulardesigned to be as transparent as possible, so that in particular theabsorption of light is as low as possible.

According to a further embodiment, the organic component, in particularan OLED, has an inverted structure. The inverted structure ischaracterized in that the cathode is located on the substrate and theother layers are disposed in a correspondingly inverted manner:

-   1. Substrate (supporting material)-   2. Cathode-   3. Electron injection layer (EIL)-   4. Electron transport layer (ETL)-   5. Hole blocking layer (HBL)-   6. Emission layer or emitting layer (EML)-   7. Electron blocking layer (EBL)-   8. Hole transport layer (HTL)-   9. Hole injection layer (HIL)-   10. anode

The presence of specific layers is merely optional. Several of theselayers can also coincide. Specific layers can also be present more thanonce in the component.

In one embodiment, in the inverted OLED, the anode layer of the typicalstructure e.g. an ITO layer (indium tin oxide), is connected as thecathode.

According to a further embodiment, the organic component, in particularan OLED, has a stacked structure. In doing so, the individual OLEDs arearranged one above the other and not next to one another as usual. Theproduction of mixed light can be made possible with the aid of a stackedstructure. This structure can be used to produce white light, forexample. To produce said white light, the entire visible spectrum istypically imaged by combining the emitted light of blue, green and redemitters. Furthermore, with practically the same efficiency andidentical luminance, significantly longer lifetimes can be achieved incomparison to conventional OLEDs. A so-called charge generation layer(CGL) between two OLEDs is optionally used for the stacked structure.Said layer consists of an n-doped and a p-doped layer, wherein then-doped layer is typically disposed closer to the anode.

In one embodiment—a so-called tandem OLED—two or more emission layersoccur between the anode and the cathode. In one embodiment, threeemission layers are arranged one above the other, wherein one emissionlayer emits red light, one emission layer emits green light and oneemission layer emits blue light, and additional charge generation,blocking or transport layers are optionally disposed between theindividual emission layers. In a further embodiment, the respectiveemission layers are disposed directly adjacent to one another. Inanother embodiment, one respective charge generation layer is situatedbetween the emission layers. Emission layers that are directly adjacentto one another and emission layers that are separated by chargegeneration layers can furthermore be combined in an OLED.

An encapsulation arrangement can furthermore be disposed above theelectrodes and the organic layers as well. The encapsulation arrangementcan, for example, be designed in the form of a glass cover or in theform of a thin-film encapsulation arrangement.

The supporting material of the optoelectronic device can, for example,be glass, quartz, plastic, metal, a silicon wafer or any other suitablesolid or flexible, optionally transparent material. The supportingmaterial can, for example, comprise one or more materials in the form ofa layer, a film, a plate or a laminate.

Transparent conductive metal oxides such as, for example, ITO (indiumtin oxide), zinc oxide, tin oxide, cadmium oxide, titanium oxide, indiumoxide or aluminum zinc oxide (AZO), Zn₂SnO₄, CdSnO₃, ZnSnO₃, MgIn₂O₄,GaInO₃, Zn₂In₂O₅ or In₄Sn₃O₁₂ or mixtures of different transparentconductive oxides, for example, can be used as the anode of theoptoelectronic device.

PEDOT:PSS (poly-3,4-ethylenedioxythiophene: polystyrene sulfonic acid),PEDOT (poly-3,4-ethylenedioxythiophene), m-MTDATA(4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD(2,2′,7,7′-tetrakis(N,N-diphenylamino)-9,9-spirobifluorene), DNTPD(4,4′-bis[N-[4-{N,N-bis(3-methyl-phenyl)amino}phenyl]-N-phenylamino]biphenyl),NPB(N,N′-bis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine),NPNPB (N,N′-diphenyl-N,N′-di-[4-(N,N-diphenyl-amino)phenyl]benzene),MeO-TPD (N,N,N′,N′-tetrakis(4-methoxyphenyl)benzene), HAT-CN(1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile) or Spiro-NPD(N,N′-diphenyl-N,N′-bis-(1-naphthyl)-9,9′-spirobifluorene-2,7-diamine),for example, are suitable materials for an HIL. The layer thickness is10-80 nm, for example. Small molecules (e.g. copper phthalocyanine (CuPce.g. 10 nm thick)) or metal oxides, such as MoO₃, V₂O₅, can also beused.

Tertiary amines, carbazole derivatives, polyethylenedioxythiophene dopedwith polystyrene sulfonic acid, polyaniline poly-TPD(poly(4-butylphenyl-diphenyl-amine)) doped with camphorsulfonic acid,[alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC(4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine]), TCTA(tris(4-carbazoyl-9-ylphenyl)amine), 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD,NPB, NPNPB, MeO-TPD, HAT-CN or TrisPcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9′H-3,3′-bicarbazole)can be used as materials for an HTL. The layer thickness is 10 nm to 100nm, for example.

The HTL can comprise a p-doped layer having an inorganic or organicdopant in an organic hole transporting matrix. Transition metal oxidessuch as vanadium oxide, molybdenum oxide or tungsten oxide, for example,can be used as the inorganic dopant. Tetrafluorotetracyanoquinodimethane(F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz) or transition metalcomplexes can, for example, be used as the organic dopants. The layerthickness is 10 nm to 100 nm, for example.

MCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP(3,3-Di(9H-carbazole-9-yl)biphenyl), tris-Pcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9′H-3,3′-bicarbazole),CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) orDCB (N,N′-dicarbazolyl-1,4-dimethylbenzene) can, for example, be used asthe materials of an electron blocking layer. The layer thickness is 10nm to 50 nm, for example.

The emitter layer EML or emission layer consists of or contains emittermaterial or a mixture comprising at least two emitter materials andoptionally one or more host materials. Suitable host materials are, forexample, mCP, TCTA, 2-TNATA, mCBP, CBP(4,4′-bis-(N-carbazolyl)-biphenyl), Sif87(dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophene-2-yl)diphenylsilane) or DPEPO(bis[2-((oxo)diphenylphosphino)phenyl]ether). The common matrixmaterials, such as CBP, are suitable for emitter material emitting inthe green or in the red range or for a mixture comprising at least twoemitter materials. UHG matrix materials (ultra-high energy gapmaterials) (see, for example, M. E. Thompson et al, Chem. Mater. 2004,16, 4743) or other so-called wide-gap matrix materials can be used foremitter material emitting in the blue range or a mixture comprising atleast two emitter materials. The layer thickness is 10 nm to 250 nm, forexample.

The hole blocking layer HBL can, for example, comprise BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=bathocuproine),bis-(2-methyl-8-hydroxyquinolinato)-(4-phenylphenolato)-aluminum(III)(BAlq), Nbphen(2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3(aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilyl-phenylphosphine oxide) or TCB/TCP(1,3,5-tris(N-carbazolyl)benzene/1,3,5-tris(carbazole)-9-yl)benzene).The layer thickness is 10 nm to 50 nm, for example.

The electron transport layer ETL can, for example, comprise materials onthe basis of AlQ₃, TSPO1, BPyTP2(2,7-di(2,2′-bipyridine-5-yl)triphenyl)), Sif87, Sif88, BmPyPhB(1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene) or BTB(4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). The layerthickness is 10 nm to 200 nm, for example.

CsF, LiF, 8-hydroxyquinolinolatolithium (Liq), Li₂O, BaF₂, MgO or NaFcan be used as materials for a thin electron injection layer EIL.

Metals or alloys, for example Al, Al>AlF, Ag, Pt, Au, Mg, Ag:Mg, can beused as materials of the cathode layer. Typical layer thicknesses are100 nm to 200 nm. In particular, one or more metals are used, which arestable when exposed to air and/or which are self-passivating, forexample by forming a thin protective oxide layer.

Aluminum oxide, vanadium oxide, zinc oxide, zirconium oxide, titaniumoxide, hafnium oxide, lanthanum oxide, tantalum oxide, for example, aresuitable materials for encapsulation. The person skilled in the art iswell aware of which combinations of materials can be used for anoptoelectronic device containing an organic molecule according to theinvention.

In one embodiment of the organic optoelectronic device according to theinvention, the organic molecule according to the invention is used asthe emission material in a light-emitting layer EML, wherein it is usedeither as a pure layer or in combination with one or more hostmaterials.

In another embodiment, the mass fraction of the organic moleculeaccording to the invention in the emitter layer EML of a light-emittinglayer in devices emitting optical light, in particular in OLEDs, isbetween 1% and 80%. In one embodiment of the organic optoelectronicdevice according to the invention, the light-emitting layer is disposedon a substrate, wherein an anode and a cathode are preferably disposedon the substrate and the light-emitting layer is disposed between theanode and the cathode.

The light-emitting layer can comprise only one organic moleculeaccording to the invention in 100% concentration, wherein the anode andthe cathode are disposed on the substrate, and the light-emitting layeris disposed between the anode and the cathode.

In one embodiment of the organic optoelectronic device according to theinvention, a hole- and electron-injecting layer is disposed between theanode and the cathode, and a hole- and electron-transporting layer isdisposed between the hole- and electron-injecting layer, and thelight-emitting layer is disposed between the hole- andelectron-transporting layer.

In another embodiment of the invention, the organic optoelectronicdevice has: a substrate, an anode, a cathode and at least one respectivehole- and electron-injecting layer, and at least one respective hole-and electron-transporting layer, and at least one light-emitting layer,the organic molecule according to the invention and one or more hostmaterials the triplet (T₁) and singlet (S₁) energy levels of which areenergetically higher than the triplet (T₁) and singlet (S₁) energylevels of the organic molecule, wherein the anode and the cathode aredisposed on the substrate, and the hole- and electron-injecting layer isdisposed between the anode and the cathode, and the hole- andelectron-transporting layer is disposed between the hole- andelectron-injecting layer, and the light-emitting layer is disposedbetween the hole- and electron-transporting layer.

In a further aspect, the invention relates to a method for producing anoptoelectronic component. To do this, an organic molecule according tothe invention is used.

In one embodiment, the production method comprises the processing of theorganic molecule according to the invention by means of a vacuumevaporation method or from a solution.

The invention also relates to a method for producing an optoelectronicdevice according to the invention, in which at least one layer of theoptoelectronic device

-   is coated using a sublimation process,-   is coated using an OVPD (organic vapor phase deposition) process,-   is coated using a carrier-gas sublimation, and/or-   is produced from solution or using a pressure process.

Known methods are used for the production of the optoelectronic deviceaccording to the invention. The layers are generally disposedindividually onto a suitable substrate in successive deposition methodsteps. The common methods, such as thermal evaporation, chemical vapordeposition (CVD), physical vapor deposition (PVD) can be used for thevapor deposition. For active matrix OLED (AMOLED) displays, depositiontakes place onto an AMOLED backplane as the substrate.

Layers can alternatively be deposited from solutions or dispersions insuitable solvents. Spin coating, dip coating and jet pressure methodsare examples of suitable coating methods. According to the invention,the individual layers can be produced via the same as well as viarespective different coating methods.

The invention will now be explained in more detail using the followingexamples without the intent to thereby restrict said invention.

EXAMPLES

General Synthesis Scheme

General Synthesis Specification AAV1:

Z1

2-bromo-4-fluorobenzonitrile (2.00 equivalent), bis(pinacolato)diboron(1.00 equivalent), pd₂(dba)₃ (0.01 equivalent), SPhos (0.04 equivalent)and potassium phosphate tribasic (6.00 equivalent) are stirred into adioxane/water mixture (ratio 10:1) at 110° C. for 16 hours undernitrogen. The reaction mixture is quenched with water and the aqueousphase is then extracted with ethylacetate. The combined organic phasesare washed with saturated NaCl solution, dried over magnesium sulfate,and the solvent is removed under reduced pressure. The product issubsequently obtained via recrystallization from toluene.

General Synthesis Specification AAV2:

Z1 (1.00 equivalent), the corresponding donor molecule D-H (2.00equivalent) and potassium phosphate tribasic (4.00 equivalent) aresuspended in DMSO under nitrogen and stirred at 110° C. (16 h). Thereaction mixture is then added to saturated sodium chloride solution andextracted three times with dichloromethane. The combined organic phasesare washed twice with saturated sodium chloride solution, dried overmagnesium sulfate, and the solvent is subsequently removed. Lastly, theraw product was purified by recrystallization from toluene. The productis obtained as a solid.

General Synthesis Specification AAV3:

Z2

2-bromo-4-fluorobenzotrifluoride (1.00 equivalent),bis(pinacolato)diboron (2.00 equivalent), pd₂(dba)₃ (0.01 equivalent),SPhos (0.04 equivalent) and potassium phosphate tribasic (6.00equivalent) are stirred into a dioxane/water mixture (ratio 10:1) at110° C. for 16 hours under nitrogen. The insoluble constituents of thereaction mixture are subsequently filtered off and washed with dioxane.The solvent of the filtrate is removed and the obtained residue isrecrystallized in toluene.

General Synthesis Specification AAV4:

Z2 (1.00 equivalent), the corresponding donor molecule D-H (2.00equivalent) and potassium phosphate tribasic (4.00 equivalent) aresuspended in DMSO under nitrogen and stirred at 110° C. (16 h). Thereaction mixture is then added to saturated sodium chloride solution andextracted three times with dichloromethane. The combined organic phasesare washed twice with saturated sodium chloride solution, dried overmagnesium sulfate, and the solvent is subsequently removed. Lastly, theraw product was purified by recrystallization from toluene. The productis obtained as a solid.

D-H in particular corresponds to a 3,6-substituted carbazole (e.g.3,6-dimethylcarbazole, 3,6-diphenylcarbazole,3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g.2,7-dimethylcarbazole, 2,7-diphenylcarbazole,2,7-di-tert-butylcarbazole), an 1,8-substituted carbazole (e.g.1,8-dimethylcarbazole, 1,8-diphenylcarbazole,1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g.1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a2-substituted carbazole (e.g. 2-methylcarbazole, 2-phenylcarbazole,2-tert-butylcarbazole) or a 3-substituted carbazole (e.g.3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

Photophysical Measurements

Pretreatment of Optical Glasses

All glasses (cuvettes and substrates made of quartz glass, diameter: 1cm) were cleaned after every use: washed three times in each case withdichloromethane, acetone, ethanol, demineralized water, placed in 5%Hellmanex solution for 24 h, thoroughly rinsed with demineralized water.The optical glasses were dried by blowing nitrogen over them.

Sample preparation, film: Spin coating

Device: Spin150, SPS Euro.

The sample concentration was equivalent to 10 mg/ml, prepared in tolueneor chlorobenzene.

Program: 1) 3 s at 400 rpm; 2) 20 s at 1000 rpm at 1000 rpm/s. 3) 10 sat 4000 rpm at 1000 rpm/s. After coating, the films were dried on a LHGprecision heating plate for 1 min at 70° C. in air.

Photoluminescence Spectroscopy and TCSPC

Steady-state emission spectroscopy was carried out using a fluorescencespectrometer of the company Horiba Scientific, Model Fluoromax-4,equipped with a 150W xenon arc lamp, excitation and emissionmonochromators and a Hamamatsu R928 photomultiplier tube, as well as a“Time-Correlated Single Photon Counting” (TCSPC) option. The emissionand excitation spectra were corrected by means of standard correctioncurves.

The emission decay times were likewise measured on this system, usingthe TCSPC method with the FM-2013 accessories and a TCSPC hub of thecompany Horiba Yvon Jobin. Excitation sources:

NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns)

NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns)

SpectraLED 310 (wavelength: 314 nm)

SpectraLED 355 (wavelength: 355 nm).

The analysis (exponential fitting) was performed using the DataStationsoftware package and the DAS6 analysis software. The fit was specifiedwith the aid of the Chi-square method

$c^{2} = {\sum\limits_{k = 1}^{i}\frac{( {e_{i} - o_{i}} )^{2}}{e_{i}}}$with e_(i): variable predicted by the fit and o_(i): measured variable.Quantum Efficiency Determination

The measurement of the photoluminescence quantum yield (PLQY) wascarried out by means of an Absolute PL Quantum Yield MeasurementC9920-03G system of the company Hamamatsu Photonics. Said systemconsists of a 150W xenon gas discharge lamp, automatically adjustableCzerny-Turner monochromators (250-950 nm) and an Ulbricht sphere with ahigh reflectance Spectralon coating (a Teflon derivative), which isconnected via a fiber optic cable to a PMA-12 multichannel detector witha BT (back-thinned)-CCD chip having 1024×122 pixels (size 24×24 μm). Theanalysis of the quantum efficiency and the CIE coordinates was carriedout using the software U6039-05 Version 3.6.0.

The emission maximum is measured in nm, the quantum yield Φ is measuredin % and the CIE color coordinates are stated as x, y values.

The photoluminescence quantum yield was determined according to thefollowing protocol:

-   1) Implementation of quality assurance measures: Anthracene in    ethanol at a known concentration serves as the reference material.-   2) Determination of the excitation wavelength: The absorption    maximum of the organic molecule was first determined and excited    with said wavelength.-   3) Implementation of the sample measurement:-   The absolute quantum yield of degassed solutions and films was    determined under a nitrogen atmosphere.

The calculation was performed within the system according to thefollowing equation:

$\Phi_{PL} = {\frac{n_{photon},{emitted}}{n_{photon},{absorbed}} = \frac{\int{{\frac{\lambda}{hc}\lbrack {{{Int}_{emitted}^{sample}(\lambda)} - {{Int}_{absorbed}^{sample}\mspace{14mu}(\lambda)}} \rbrack}d\;\lambda}}{\int{{\frac{\lambda}{hc}\lbrack {{{Int}_{emitted}^{reference}(\lambda)} - {{Int}_{absorbed}^{reference}\mspace{11mu}(\lambda)}} \rbrack}d\;\lambda}}}$with the photon number n_(photon) and the intensity Int.

Production and characterization of organic electroluminescence devicesfrom the gas phase With the organic molecules according to theinvention, OLED devices can be produced by means of vacuum sublimationtechniques.

These not yet optimized OLEDs can be characterized in the usual manner.To do this, the electroluminescence spectra, the external quantumefficiency (measured in %) as a function of the brightness andcalculated from the light detected by the photodiode, theelectroluminescence spectra and the current are recorded.

Example 1

Example 1 was produced in accordance with AAV1 (Yield 72%) and AAV2(Yield 78%).

¹H NMR (500 MHz, chloroform-d) δ 8.07 (d, 2H, Ar—H), 7.90-7.86 (m, 6H,Ar—H), 7.85 (dd, 2H, Ar—H), 7.56 (d, 4H, Ar—H), 7.27-7.25 (m, 4H, Ar—H),2.53 (s, 12H, CH₃) ppm.

FIG. 1 shows the emission spectrum of Example 1 (10% in PMMA). Theemission maximum is at 448 nm. The photoluminescence quantum yield(PLQY) is 68% and the full width at half maximum is 0.45 eV. The CIE_(x)color coordinate is 0.16 and the CIE_(y) color coordinate is 0.13.

Example 2

Example 2 was produced in accordance with AAV1 (Yield 72%) and AAV2(Yield 96%). Thin layer chromatography: R_(f)=0.66(cyclohexane/ethylacetate 5:1)

FIG. 2 shows the emission spectrum of Example 2 (10% in PMMA). Theemission maximum is at 442 nm. The photoluminescence quantum yield(PLQY) is 69% and the full width at half maximum is 0.47 eV. The CIE_(x)color coordinate is 0.16 and the CIE_(y) color coordinate is 0.10.

Example 3

Example 3 was produced in accordance with AAV1 (Yield 72%) and AAV2(Yield 33%).

FIG. 3 shows the emission spectrum of Example 3 (10% in PMMA). Theemission maximum is at 487 nm. The photoluminescence quantum yield(PLQY) is 58% and the full width at half maximum is 0.48 eV. The CIE_(x)color coordinate is 0.21 and the CIE_(y) color coordinate is 0.35.

Example 4

Example 4 was produced in accordance with AAV1 (Yield 72%) and AAV2.

Thin layer chromatography: R_(f)=0.19 (cyclohexane/ethylacetate 5:1)

FIG. 4 shows the emission spectrum of Example 4 (10% in PMMA). Theemission maximum is at 444 nm. The photoluminescence quantum yield(PLQY) is 34% and the full width at half maximum is 0.52 eV. The CIE_(x)color coordinate is 0.19 and the CIE_(y) color coordinate is 0.17.

Example 5

Example 5 was produced in accordance with AAV1 (Yield 72%) and AAV2.

Thin layer chromatography: R_(f)=0.56 (cyclohexane/ethylacetate 5:1)

FIG. 5 shows the emission spectrum of Example 5 (10% in PMMA). Theemission maximum is at 509 nm. The photoluminescence quantum yield(PLQY) is 57% and the full width at half maximum is 0.51 eV. Theemission decay time was determined to be 21.6 μs. The CIE_(x) colorcoordinate is 0.27 and the CIE_(y) color coordinate is 0.46.

Example 6

Example 6 was produced with reaction conditions analogous to thosedescribed in AAV1 and AAV2, wherein2-bromo-4-fluoro-3-methylbenzonitrile was used as the educt instead of2-bromo-4-fluorobenzonitrile.

¹H NMR (500 MHz, chloroform-d) δ 7.95-7.93 (m, 6H, Ar—H), 7.71 (s, 2H,Ar—H), 7.28-7.21 (m, 4H, Ar—H), 7.06 (bs, 4H, Ar—H), 2.57 (s, 12H, CH₃),2.16 (s, 6H, CH₃) ppm.

FIG. 6 shows the emission spectrum of Example 6 (10% in PMMA). Theemission maximum is at 434 nm. The photoluminescence quantum yield(PLQY) is 35% and the full width at half maximum is 0.49 eV.

Example D1

Example 2 was tested in an OLED component (Component X1) with thefollowing structure (the fraction of the molecule according to theinvention in the emission layer is stated in percent by weight,substrate glass):

Layer Thickness 10 100 nm Al 9 2 nm Liq 8 30 nm TPBi 7 10 nm DPEPO 6 20nm 2 (30%):DPEPO 5 10 nm CzSi 4 20 nm TCTA 3 50 nm NPB 2 20 nm m-MTDATA1 120 nm ITO

The following values were determined:

Emission maximum: 441 nm Maximum output efficiency: 6 0 ± 1.7 lm/WMaximum current efficiency: 12.4 ± 3.3 cd/A CIE: CIEx: 0.16 CIEy: 0.13at 14 V Maximum external quantum 11.3 ± 2.7% yield (EQE):

Further examples of organic molecules having a structure according toFormula I:

Although illustrative embodiments of the present invention have beendescribed herein with reference to the accompanying drawings, it is tobe understood that the invention is not limited to those preciseembodiments, and that various other changes and modifications may bemade by one skilled in the art without departing from the scope orspirit of the invention.

The invention claimed is:
 1. An organic molecule, comprising a structureof Formula I:

with X=CN or CF3, and D=

wherein # is the point of attachment of unit D to one of the phenylrings shown in Formula I; Z is a direct bond or is selected from thegroup consisting of CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O, SiR³R⁴, S, S(O)and S(O)₂; in each occurrence R¹ and R² are the same or different andare selected from the group consisting of: H, deuterium; a linear alkylgroup having 1 to 5 C atoms, wherein one or more H atoms can be replacedby deuterium; a linear alkenyl or alkynyl group having 2 to 8 C atoms,wherein one or more H atoms can be replaced by deuterium; a branched orcyclic alkyl, alkenyl or alkynyl group having 3 to 10 C atoms, whereinone or more H atoms can be replaced by deuterium; and an aromatic ringsystem having 5 to 15 aromatic ring atoms, which can in each case besubstituted with one or more radicals R⁶; in each occurrence R^(a), R³and R⁴ are the same or different and are selected from the groupconsisting of: H, deuterium, N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃,CN, F, Br, I, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40C atoms, which can in each case can be substituted with one or moreradicals R⁵, wherein one or more non-adjacent CH₂ groups can be replacedby R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵,P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵ and wherein one or more H atomscan be replaced by deuterium, CN, CF₃ or NO₂; a linear alkenyl oralkynyl group having 2 to 40 C atoms, which can in each case besubstituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂,Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, Sor CONR⁵ and wherein one or more H atoms can be replaced by deuterium,CN, CF₃ or NO₂; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy orthioalkoxy group having 3 to 40 C atoms, which can in each case besubstituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂,Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, Sor CONR⁵ and wherein one or more H atoms can be replaced by deuterium,CN, CF₃ or NO₂; an aromatic or heteroaromatic ring system having 5 to 60aromatic ring atoms, which can in each case be substituted with one ormore radicals R⁵; an aryloxy or heteroaryloxy group having 5 to 60aromatic ring atoms, which can be substituted with one or more radicalsR⁵; and a diarylamino group, diheteroarylamino group orarylheteroarylamino group having 10 to 40 aromatic ring atoms, which canbe substituted with one or more radicals R⁵; in each occurrence R⁵ isthe same or different and is selected from the group consisting of: H,deuterium, N(R⁶)₂, OH, Si(R⁶)₃, B(OR⁶)₂, OSO₂R⁶, CF₃, CN, F, Br, I, alinear alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, whichcan in each case be substituted with one or more radicals R⁶, whereinone or more non-adjacent CH₂ groups can be replaced by R⁶C═CR⁶, C≡C,Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂,NR⁶, O, S or CONR⁶ and wherein one or more H atoms can be replaced bydeuterium, CN, CF₃ or NO₂; a linear alkenyl or alkynyl group having 2 to40 C atoms, which can in each case be substituted with one or moreradicals R⁶, wherein one or more non-adjacent CH₂ groups can be replacedby R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶,P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶ and wherein one or more H atomscan be replaced by deuterium, CN, CF₃ or NO₂; a branched or cyclicalkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 Catoms, which can in each case be substituted with one or more radicalsR⁶, wherein one or more non-adjacent CH₂ groups can be replaced byR⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶,P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶ and wherein one or more H atomscan be replaced by deuterium, CN, CF₃ or NO₂; an aromatic orheteroaromatic ring system having 5 to 60 aromatic ring atoms, which canin each case be substituted with one or more radicals R⁶; an aryloxy orheteroaryloxy group having 5 to 60 aromatic ring atoms, which can besubstituted with one or more radicals R⁶; and a diarylamino group,diheteroarylamino group or arylheteroarylamino group having 10 to 40aromatic ring atoms, which can be substituted with one or more radicalsR⁶; in each occurrence R⁶ is the same or different and is selected fromthe group consisting of: H, deuterium, OH, CF₃, CN, F, Br, I, a linearalkyl, alkoxy or thioalkoxy group having 1 to 5 C atoms, wherein one ormore H atoms can be replaced by deuterium, CN, CF₃ or NO₂; a linearalkenyl or alkynyl group having 2 to 5 C atoms, wherein one or more Hatoms can be replaced by deuterium, CN, CF₃ or NO₂; a branched or cyclicalkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 5 Catoms, wherein one or more H atoms can be replaced by deuterium, CN, CF₃or NO₂; an aromatic or heteroaromatic ring system having 5 to 60aromatic ring atoms; an aryloxy or heteroaryloxy group having 5 to 60aromatic ring atoms; and a diarylamino group, diheteroarylamino group orarylheteroarylamino group having 10 to 40 aromatic ring atoms; whereineach of the radicals R^(a), R³, R⁴ or R⁵ can also form a mono- orpolycyclic, aliphatic, aromatic and/or benzoannelated ring system withone or more further radicals R^(a), R³, R⁴ or R⁵; and wherein at leastone R^(a) is not H, and wherein at least one R² is H.
 2. The organicmolecule according to claim 1, wherein R¹ is H or methyl and R² is H. 3.The organic molecule according to claim 1, wherein both X are CN.
 4. Theorganic molecule according to claim 1, wherein D comprises a structureof Formula IIa:

wherein # and R^(a) have the aforestated meanings.
 5. The organicmolecule according to claim 1, wherein D comprises a structure ofFormula

wherein in each occurrence R^(b) is the same or different and isselected from the group consisting of: N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 C atoms, which can in each case be substituted with oneor more radicals R⁵, wherein one or more non-adjacent CH₂ groups can bereplaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se,C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵ and wherein one or more Hatoms can be replaced by deuterium, CN, CF₃ or NO₂; a linear alkenyl oralkynyl group having 2 to 40 C atoms, which can in each case besubstituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂,Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, Sor CONR⁵ and wherein one or more H atoms can be replaced by deuterium,CN, CF₃ or NO₂; a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy orthioalkoxy group having 3 to 40 C atoms, which can in each case besubstituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂,Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, Sor CONR⁵ and wherein one or more H atoms can be replaced by deuterium,CN, CF₃ or NO₂; an aromatic or heteroaromatic ring system having 5 to 60aromatic ring atoms, which can in each case be substituted with one ormore radicals R⁵; an aryloxy or heteroaryloxy group having 5 to 60aromatic ring atoms, which can be substituted with one or more radicalsR⁵; and a diarylamino group, diheteroarylamino group orarylheteroarylamino group having 10 to 40 aromatic ring atoms, which canbe substituted with one or more radicals R⁵; and # and R⁵ have theaforestated meanings.
 6. The organic molecule according to claim 1,wherein D comprises a structure of Formula IIc:

wherein in each occurrence R^(b) is the same or different and isselected from the group consisting of: N(R⁵)₂, OH, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I; a linear alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 C atoms, which can in each case be substituted with oneor more radicals R⁵, wherein one or more non-adjacent CH₂ groups can bereplaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se,C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵ and wherein one or more Hatoms can be replaced by deuterium, CN, CF₃ or NO₂; a linear alkenyl oralkynyl group having 2 to 40 C atoms, which can in each case besubstituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R5)2,^(Ge(R)5)2, ^(Sn(R)5)2, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵,O, S or CONR⁵ and wherein one or more H atoms can be replaced bydeuterium, CN, CF₃ or NO₂; a branched or cyclic alkyl, alkenyl, alkynyl,alkoxy or thioalkoxy group having 3 to 40 C atoms, which can in eachcase be substituted with one or more radicals R⁵, wherein one or morenon-adjacent CH₂ groups can be replaced by R⁵C═CR⁵, C≡C, Si(R⁵)₂,Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, Sor CONR⁵ and wherein one or more H atoms can be replaced by deuterium,CN, CF₃ or NO₂; an aromatic or heteroaromatic ring system having 5 to 60aromatic ring atoms, which can in each case be substituted with one ormore radicals R⁵; an aryloxy or heteroaryloxy group having 5 to 60aromatic ring atoms, which can be substituted with one or more radicalsR⁵; and a diarylamino group, diheteroarylamino group orarylheteroarylamino group having 10 to 40 aromatic ring atoms, which canbe substituted with one or more radicals R⁵; and # and R⁵ have theaforestated meanings.
 7. The organic molecule according to claim 5,wherein in each occurrence R^(b) is the same or different and isselected from the group consisting of: Me, ^(i)Pr, ^(t)Bu, CN, CF₃; Ph,which can in each case be substituted with one or more radicals selectedfrom Me, ^(i)Pr, ^(t)Bu, CN, CF₃, or Ph; pyridinyl, which can in eachcase be substituted with one or more radicals selected from Me, ^(i)Pr,^(t)Bu, CN, CF₃, or Ph; pyrimidinyl which can in each case besubstituted with one or more radicals selected from Me, ^(i)Pr, ^(t)Bu,CN, CF₃, or Ph; carbazolyl which can in each case be substituted withone or more radicals selected from Me, ^(i)Pr, ^(t)Bu, CN, CF₃, or Ph;and N(Ph)₂.
 8. A method for producing an organic molecule according toclaim 1, wherein a in 6 position R¹-substituted and in 3 and 5 positionR²-substituted 2-bromo-4-fluorobenzonitrile or a in 6 positionR¹-substituted and in 3 and 5 position R²-substituted2-bromo-4-fluorobenzotrifluoride is used as the educt.
 9. Anoptoelectronic device comprising an organic molecule according toclaim
 1. 10. The optoelectronic device according to claim 9, wherein theoptoelectronic device is an organic light-emitting diode, alight-emitting electrochemical cell, an organic light-emitting sensor,an organic diode, an organic solar cell, an organic transistor, anorganic field-effect transistor, an organic laser or a down-conversionelement.
 11. A composition comprising: (a) at least one organic moleculeaccording to claim 1, as an emitter and/or host; (b) one or more emitterand/or host materials different from the at least one organic moleculeaccording to claim 1; and (c) optionally one or more dyes and/or one ormore solvents.
 12. An optoelectronic device comprising the compositionaccording to claim
 11. 13. The optoelectronic device according to claim12, comprising: a substrate; an anode; and a cathode, wherein the anodeor the cathode is disposed on the substrate; and at least onelight-emitting layer disposed between the anode and the cathode andwhich comprises the composition.
 14. The optoelectronic device accordingto claim 9, wherein the organic molecule is one of an emitter and a hostin the optoelectronic component.
 15. The optoelectronic device accordingto claim 10, wherein the organic molecule is one of an emitter and ahost in the optoelectronic component.
 16. The optoelectronic deviceaccording to claim 14, wherein the proportion of the organic molecule inthe emitter or the host is in the range of 1% to 80%.
 17. Theoptoelectronic device according to claim 9, comprising: a substrate; ananode; a cathode, wherein the anode or the cathode is applied to thesubstrate; and at least one light-emitting layer disposed between theanode and the cathode and which comprises the organic molecule.
 18. Theorganic molecule according to claim 2, wherein both X are CN.
 19. Theorganic molecule according to claim 6, wherein in each occurrence R^(b)is the same or different and is selected from the group consisting of:wherein in each occurrence R^(b) is the same or different and isselected from the group consisting of: Me, ^(i)Pr, ^(t)Bu, CN, CF₃; Ph,which can in each case be substituted with one or more radicals selectedfrom Me, ^(i)Pr, ^(t)Bu, CN, CF₃, or Ph; pyridinyl, which can in eachcase be substituted with one or more radicals selected from Me, ^(i)Pr,^(t)Bu, CN, CF₃, or Ph; pyrimidinyl which can in each case besubstituted with one or more radicals selected from Me, ^(i)Pr, ^(t)Bu,CN, CF₃, or Ph; carbazolyl which can in each case be substituted withone or more radicals selected from Me, ^(i)Pr, ^(t)Bu, CN, CF₃, or Ph;and N(Ph)₂.
 20. A process for producing an optoelectronic component,comprising processing of the organic molecule according to claim 1 by avacuum vaporization process or from a solution.